This invention relates to tertiary hydroxyl carboxaldehydes defined according to the structure: ##STR8## wherein the lines ##STR9## represent covalent carbon-carbon bonds when m does not=0; and wherein the lines ##STR10## do not represent any bonds when m=0; wherein R represents hydrogen or methyl; wherein p and q each represents 0 or 1 with the proviso that p=1 when q=0 and p=0 when q=1; wherein X and Z each represent one or more carbon atoms required to complete a bicyclo ring with the lines ##STR11## representing carbon-carbon bonds; wherein X and Z complete a phenyl moiety when the line ##STR12## represents no bond; wherein X and Z complete a cycloalkyl ring moiety with the lines ##STR13## represent carbon-carbon bonds and with the line ##STR14## representing no bond; and wherein when m is 0, X represents an alkylene moiety, produced according to an oxo reaction on a member of the unsaturated genus having the structure: ##STR15## and organoleptic uses thereof particularly augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles.
Inexpensive chemical compounds which can provide woody, nutty, floral, lilac, green, peach-like, balsamic and fresh air dried linen aromas with minty, floral, cinnamon-like and green topnotes are highly desirable in the art of perfumery. Many of the natural materials which provide such fragrances and contribute such desired nuances to perfumery compositions and perfumed articles are high in cost, unobtainable at times, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
There is, accordingly, a continuing effort to find synthetic materials which will replace, enhance or augment the fragrance notes provided by natural essential oils or compositions thereof. Unfortunately, many of the synthetic materials either have the desired nuances only to a relatively small degree, or they contribute undesirable or unwanted odor to the compositions.
U.S. Pat. No. 4,357,247 issued on Nov. 2, 1982 discloses aliphatic C.sub.11 branched chain aldehydes and alcohols, defined according to the generic structure: ##STR16## wherein one of X.sub.1 or X.sub.2 is hydrogen and the other of X.sub.1 or X.sub.2 is methyl; and wherein one of Z.sub.1 or Z.sub.2 is hydrogen and the other of Z.sub.1 or Z.sub.2 is hydroxymethyl having the structure: ##STR17## or carboxaldehyde having the structure: ##STR18## for use in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles. The resulting compounds and compositions of matter provide citrusy, green, melony, woody, peanut oil-like and vetiver-like aroma nuances. The compounds of U.S. Pat. No. 4,357,247 are different in kind insofar as their structure and organoleptic properties are concerned from the compounds of the instant application.
Furthermore, C.sub.11 aliphatic alcohols and aldehydes are well known in the art of perfumery, e.g., n-undecanal and n-undecanol. Oxo reaction products on hydrocarbon compounds are also well known in the perfumery industry aside from U.S. Pat. No. 4,357,247. Thus, U.S. Pat. No. 4,146,505 discloses the formation of hydroxymethyl-formyl-tricyclo[5,2,1,0.sup.2,6 ]decane having the structure: ##STR19## wherein R.sub.1 and R.sub.2 are the hydroxymethyl group, CH.sub.2 OH or the formyl group CHO and R.sub.1 represents CH.sub.2 OH when R.sub.2 is CHO and vice versa. This polycyclic carboxaldehyde alcohol is indicated to be useful as a musk aroma imparting or augmenting material. The material is indicated to be produced by reaction of carbon monoxide and hydrogen with dicyclopentadiene. Other oxo reaction products on unsaturated hydrocarbons are known in the perfumery industry, for example, "Vandor-B", which is the oxo reaction product of carbon monoxide and hydrogen on diiosbutylene. This material has been produced by International Flavors & Fragrances Inc., the assignee of the instant patent application, for several years.
Nothing in the prior art however, discloses the compounds defined according to the structure: ##STR20## produced by oxo reaction on compounds defined according to the structure: ##STR21## wherein the lines ##STR22## represent covalent carbon-carbon bonds when m does not=0; and wherein the lines ##STR23## do not represent any bonds when m=0; wherein R represents hydrogen or methyl; wherein p and q each represents 0 or 1 with the proviso that p=1 when q=0 and p=0 when q=1;
wherein X and Z each represent one or more carbon atoms required to complete a bicyclo ring with the lines ##STR24## representing carbon-carbon bonds; wherein X and Z complete a phenyl moiety when the line ##STR25## represents no bond; wherein X and Z complete a cycloalkyl ring moiety with the lines ##STR26## represent carbon-carbon bonds and with the line ##STR27## representing no bond; and wherein when m is 0, X represents an alkylene moiety.